Luxury rentals in The Great Lakes

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Top-rated vacation rentals in The Great Lakes

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Villa in Chicago, Illinois

Chicago Gold Coast Luxury Home

This apartment is nestled onto a quiet tree-lined street in Chicago’s coveted Gold Coast neighborhood. Enjoy access to a fitness center and a common sundeck when the sun is shining and you want to relax outdoors. Don’t feel like cooking? A taste of the city’s high-end restaurants and lively bars are at your doorstep. Scenic parks, picturesque Oak Street Beach, museums, and more await nearby. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower and bathtub, Walk-in closet, Television • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower and bathtub, Television • Bedroom 3: King size bed, Ensuite bathroom with stand-alone shower • Bedroom 4: King size bed, Ensuite bathroom with stand-alone shower • Bedroom 5: Queen size bed, 2 Twin size beds, Ensuite bathroom with stand-alone shower FEATURES & AMENITIES • Decorative fireplace • More under “What this place offers” below STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions • Housekeeping • More under “Add-on services” below

Mar 23 – 30

$4,480 per night

Villa in Caledon, Canada

Peak House

Hills and valleys stretch for 100 acres around this design-forward hilltop home in the Ontario countryside. A pool and hot tub sit mid-lawn, and a firepit anchors a covered outdoor seating area. Glass walls contrast moody rooms splashed with dark stone and wood paneling. It’s a few minutes to the village of Caledon and less than an hour to dining, shopping, and entertainment in downtown Toronto. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Master: King size bed, Ensuite bathroom with standalone shower and bathtub • Bedroom 2: Queen size bed • Bedroom 3: Twin size bed, Shared access to bathroom • Bedroom 4: 2 Twin over bunk beds, Ensuite bathroom with standalone shower • Bedroom 5: Queen size bed, Shared access to bathroom FEATURES & AMENITIES • Formal dining area with seating for 8 • More under “What this place offers” below OUTDOOR FEATURES • Terrace • More under “What this place offers” below STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions • Housekeeping • More under “Add-on services” below

Aug 22 – 29

$7,538 per night

Place to stay in Caledon, Canada

Peak House

Hills and valleys stretch for 100 acres around this design-forward hilltop home in the Ontario countryside. A pool and hot tub sit mid-lawn, and a firepit anchors a covered outdoor seating area. Glass walls contrast moody rooms splashed with dark stone and wood paneling. It’s a few minutes to the village of Caledon and less than an hour to dining, shopping, and entertainment in downtown Toronto. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Master: King size bed, Ensuite bathroom with standalone shower and bathtub • Bedroom 2: Queen size bed • Bedroom 3: Twin size bed, Shared access to hallway bathroom, • Bedroom 4: 2 Twin over bunk beds, Ensuite bathroom with standalone shower • Bedroom 5: Queen size bed, Shared access to hallway bathroom, STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Apr 19 – 26

$7,538 per night

Place to stay in Toronto, Canada

SoHo Residences One Bedroom Premier King Suite

Please note that this home is in close proximity to an ongoing construction project. Please inquire with a Trip Designer for more information. Skyline meets sleek interiors at this heart-of-the-city suite in the Entertainment District. Guests are welcome at the complex’s shared gym and rooftop terrace. Wall-to-wall windows flood the open-plan living area with light and city views, and vintage bills act as framed artwork. It’s a short walk to restaurants, shops, and nightlife in downtown Toronto. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower and bathtub, walk-in closet, Kitchen, Television SERVICES INCLUDED Concierge services • More under “What this place offers” below SHARED ACCESS TO HOTEL AMENITIES Health Club Moretti Restaurant Moretti Caffe

Mar 9 – 16

$454 per night

Home in Nobleton, Canada

King Vista

This Scandinavian inspired vacation home is the perfect escape from the city. Located just 40 km north of Toronto, you will feel like you're a million miles away but within an hour's drive. This brand new sustainably built home invites you to come and enjoy the nature of the 50 acre estate while minimizing your carbon footprint. With endless nearby hiking trails, a heated saltwater pool and hot tub, everything is here for your enjoyment! Copyright © Luxury Retreats. All rights reserved.

Feb 25 – Mar 4

$5,651 per night

Villa in Innisfil, Canada

5.0 out of 5 average rating, 11 reviews

Luxury Lake Simcoe Waterfront Cottage

Welcome to our lakefront vacation rental! Enjoy the full spectrum of morning golden hour colours in this premium waterfront villa on Lake Simcoe. This premium house on a private road is situated in a quiet neighbourhood, which offers a peaceful environment for time well spent with a group of friends or large family gatherings. This house is a unique east-facing spot surrounded by greenery and fresh air. It is minutes from happening Friday Harbour resort.

Dec 30 – Jan 6

$1,866 per night

Aparthotel in Toronto, Canada

SoHo Residences Two Bedroom King Suite

Glass towers reflect back park scenery outside this heart-of-downtown suite. Guests are welcome to use the shared gym and rooftop terrace, and can book meeting rooms. Black and charcoal tones give a sleek feel to suit the urban setting; floor-to-ceiling windows showcase city views. It’s a short walk from the complex to restaurants, shops, nightlife, and more in Toronto’s Entertainment District. Copyright © Luxury Retreats. All rights reserved.

May 2 – 9

$579 per night

Place to stay in Brechin, Canada

Lake Simcoe Haven

Designer 4,000 sqft cottage w/ 5 bedroom (6 BEDS)/3.5 bathroom & over 100ft of water frontage on the canal leading to Lake Simcoe has excellent boat access & room to dock up to two large boats faces a breathtaking lakefront view, ideal for year-round cottage getaways. Less than 1.5 hour drive from the GTA/Toronto. This cottage is perfect for weekend getaways, bike trails, water activities, and fishing

Mar 16 – 23

$1,125 per night

Apartment in Chicago, Illinois

Cloud9 | Indoor Pool| View to The Bean|The Orion

Welcome to The Orion! Guests must pass screening with ID. A $5,000 USD SECURITY DEPOSIT HOLD on major credit cards is required as per House Rules. Spanning 2662ft²/247m², this Penthouse located in The Loop is close to Millenium Park, Prudential Palaza, Chicago Cultural Center, Chicago Architecture Center, Riverwalk 100 W.

Sep 20 – 27

$2,134 per night

Apartment in Chicago, Illinois

5.0 out of 5 average rating, 3 reviews

Cloud9|XL Penthouse near the Bean| The Stella

Welcome to The Stella! Guests must pass screening with ID. A $5,000 USD SECURITY DEPOSIT HOLD on major credit cards is required as per House Rules. Spanning 2643ft²/246m², this Penthouse located in The Loop is close to Millenium Park, Prudential Plaza, Chicago Cultural Center, Chicago Architecture Center, Riverwalk 100 W

Mar 25 – Apr 1

$2,528 per night